Ethanol → 1-Methyl-1,4,5,6-Tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

HRID 1681876Notes

Reaction equation

HRID 1681876 reaction equation
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[CH3:8][N:9]1[CH2:14][CH:13]([C:15](OC)=O)[CH2:12][N:11]=[CH:10]1.C(O)C>C1COCC1>[CH3:8][N:9]1[CH2:14][CH:13]([C:15]2[O:7][N:6]=[C:3]([CH3:4])[N:5]=2)[CH2:12][N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 152943851-Methyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Product 1

HCID 152943861-Methyl-1,4,5,6-Tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil 112 mg, 2.8 mmol) and acetamidoxime (207 mg, 2.8 mmol) are suspended in dry THF (16 ml) in an oven dried round bottom flask under nitrogen with stirring at 0° C. After 10 minutes the grey suspension is refluxed for 30 minutes giving a white suspension. 1-Methyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (593 mg, 2.8 mmol) dissolved in dry THF (4 ml) and anhydrous ethanol (1 ml) is added via syringe and reflux continued 15 hours. The suspension is evaporated in vacuo to a yellow gum and chromatographed (silica, chloroform/methanol, 9:1) to yield 24 mg (rf=0.07, 4%) solids identified by 300 MHz nmr and ms m/z=180.

Workup

  1. customdried round bottom flask under nitrogen
  2. temperatureAfter 10 minutes the grey suspension is refluxed for 30 minutes
  3. customgiving a white suspension
  4. temperaturereflux
  5. customThe suspension is evaporated in vacuo to a yellow gum
  6. customchromatographed (silica, chloroform/methanol, 9:1)
  7. customto yield 24 mg (rf=0.07, 4%) solids

Sources & evidence

ORD record
ord-b5dcbb4cbfa843c3bfd8c01681952cef
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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